{"title":"拟南芥中顺式-OPDA-α-单甘酯的分离与结构测定","authors":"Shotaro Hirota, Yusuke Ito, Shiro Inoue, Naoki Kitaoka, Tohru Taniguchi, Kenji Monde, Kosaku Takahashi and Hideyuki Matsuura*, ","doi":"10.1021/acs.jnatprod.3c01237","DOIUrl":null,"url":null,"abstract":"<p ><i>cis</i>-12-oxo-Phytodieneoic acid-α-monoglyceride (<b>1</b>) was isolated from <i>Arabidopsis thaliana</i>. The chemical structure of <b>1</b> was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the <i>cis</i>-OPDA moiety in <b>1</b> was determined by comparison of <sup>1</sup>H NMR spectra and ECD measurements. With respect to the absolute configuration of the β-position of the glycerol backbone, the 2:3 ratio of (<i>S</i>) to (<i>R</i>) was determined by making ester-bonded derivatives with (<i>R</i>)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride and comparing <sup>1</sup>H NMR spectra. Wounding stress did not increase endogenous levels of <b>1</b>, and it was revealed <b>1</b> had an inhibitory effect of <i>A. thaliana</i> post germination growth. Notably, the endogenous amount of <b>1</b> was higher than the amounts of (+)-7-<i>iso</i>-jasmonic acid and (+)-<i>cis</i>-OPDA in intact plants. <b>1</b> also showed antimicrobial activity against Gram-positive bacteria, but jasmonic acid did not. It was also found that α-linolenic acid-α-monoglyceride was converted into <b>1</b> in the <i>A. thaliana</i> plant, which implied α-linolenic acid-α-monoglyceride was a biosynthetic intermediate of <b>1</b>.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana\",\"authors\":\"Shotaro Hirota, Yusuke Ito, Shiro Inoue, Naoki Kitaoka, Tohru Taniguchi, Kenji Monde, Kosaku Takahashi and Hideyuki Matsuura*, \",\"doi\":\"10.1021/acs.jnatprod.3c01237\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p ><i>cis</i>-12-oxo-Phytodieneoic acid-α-monoglyceride (<b>1</b>) was isolated from <i>Arabidopsis thaliana</i>. The chemical structure of <b>1</b> was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the <i>cis</i>-OPDA moiety in <b>1</b> was determined by comparison of <sup>1</sup>H NMR spectra and ECD measurements. With respect to the absolute configuration of the β-position of the glycerol backbone, the 2:3 ratio of (<i>S</i>) to (<i>R</i>) was determined by making ester-bonded derivatives with (<i>R</i>)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride and comparing <sup>1</sup>H NMR spectra. Wounding stress did not increase endogenous levels of <b>1</b>, and it was revealed <b>1</b> had an inhibitory effect of <i>A. thaliana</i> post germination growth. Notably, the endogenous amount of <b>1</b> was higher than the amounts of (+)-7-<i>iso</i>-jasmonic acid and (+)-<i>cis</i>-OPDA in intact plants. <b>1</b> also showed antimicrobial activity against Gram-positive bacteria, but jasmonic acid did not. It was also found that α-linolenic acid-α-monoglyceride was converted into <b>1</b> in the <i>A. thaliana</i> plant, which implied α-linolenic acid-α-monoglyceride was a biosynthetic intermediate of <b>1</b>.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-04-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Natural Products \",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jnatprod.3c01237\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jnatprod.3c01237","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana
cis-12-oxo-Phytodieneoic acid-α-monoglyceride (1) was isolated from Arabidopsis thaliana. The chemical structure of 1 was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the cis-OPDA moiety in 1 was determined by comparison of 1H NMR spectra and ECD measurements. With respect to the absolute configuration of the β-position of the glycerol backbone, the 2:3 ratio of (S) to (R) was determined by making ester-bonded derivatives with (R)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride and comparing 1H NMR spectra. Wounding stress did not increase endogenous levels of 1, and it was revealed 1 had an inhibitory effect of A. thaliana post germination growth. Notably, the endogenous amount of 1 was higher than the amounts of (+)-7-iso-jasmonic acid and (+)-cis-OPDA in intact plants. 1 also showed antimicrobial activity against Gram-positive bacteria, but jasmonic acid did not. It was also found that α-linolenic acid-α-monoglyceride was converted into 1 in the A. thaliana plant, which implied α-linolenic acid-α-monoglyceride was a biosynthetic intermediate of 1.
期刊介绍:
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.